EP3156458B1 - Bei zimmertemperatur härtbare organopolysiloxanzusammensetzung und formprodukt mit gehärtetem produkt aus der besagten, bei zimmertemperatur härtbaren organopolysiloxanzusammensetzung - Google Patents

Bei zimmertemperatur härtbare organopolysiloxanzusammensetzung und formprodukt mit gehärtetem produkt aus der besagten, bei zimmertemperatur härtbaren organopolysiloxanzusammensetzung Download PDF

Info

Publication number
EP3156458B1
EP3156458B1 EP15809931.7A EP15809931A EP3156458B1 EP 3156458 B1 EP3156458 B1 EP 3156458B1 EP 15809931 A EP15809931 A EP 15809931A EP 3156458 B1 EP3156458 B1 EP 3156458B1
Authority
EP
European Patent Office
Prior art keywords
group
component
parts
room
temperature
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP15809931.7A
Other languages
English (en)
French (fr)
Other versions
EP3156458A4 (de
EP3156458A1 (de
Inventor
Takahiro Yamaguchi
Takafumi Sakamoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shin Etsu Chemical Co Ltd
Original Assignee
Shin Etsu Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shin Etsu Chemical Co Ltd filed Critical Shin Etsu Chemical Co Ltd
Publication of EP3156458A1 publication Critical patent/EP3156458A1/de
Publication of EP3156458A4 publication Critical patent/EP3156458A4/de
Application granted granted Critical
Publication of EP3156458B1 publication Critical patent/EP3156458B1/de
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5425—Silicon-containing compounds containing oxygen containing at least one C=C bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C08K5/57—Organo-tin compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure

Definitions

  • the present invention relates to a room-temperature-curable organopolysiloxane composition and an elastomeric moulded product (a cured silicone rubber product) obtained by curing the room-temperature-curable organopolysiloxane.
  • the present invention relates to a room-temperature-curable organopolysiloxane composition comprising, as a curing agent (a crosslinking agent), an organic silicon compound having, within the molecule, a hydrolyzable silyl group and a structure of 2 silicon atoms crosslinked by a carbon-carbon double bond, and a moulded product obtained by curing the room-temperature-curable organopolysiloxane composition.
  • Typical examples of the dealcoholization-type organopolysiloxane compositions include a composition composed of a polyorganosiloxane end-capped with a hydroxyl group, an alkoxysilane, and an organic titanium compound; a composition composed of a polyorganosiloxane end-capped with an alkoxysilyl group, an alkoxysilane, and an alkoxy titanium; a composition composed of a linear polyorganosiloxane the terminal of which has been blocked by an alkoxysilyl group containing a silethylene group, an alkoxysilane, and an alkoxy titanium; and a composition composed of a polyorganosiloxane end-capped with a hydroxyl group or a polyorganosiloxane end-capped with an alkoxy group and an alkoxy- ⁇ -silyl ester compound (Patent Literatures 1 to 4).
  • JPS5488225 discloses a crosslinking agent for a polyorganosiloxane.
  • the agent is a cis-1,2-disilylalkylene.
  • organosiloxane polymers having a reactive (hydrolyzable) alkoxysilyl group at its end have been conventionally known. Because being end-capped with an alkoxysilyl group, these polymers are unlikely to have their curability subjected to changes (degradation) with time and therefore have excellent storage stability. In addition, these polymers have their workability (viscosity, thixotropy) optionally controllable, crosslink to each other upon reaction with moisture in the air and give an elastomer, and have excellent properties (hardness, tensile strength, elongation at break).
  • the dealcoholization-type organopolysiloxane compositions compared to conventionally known other types of organosiloxane compositions such as deoximation type, deacetic acid type, and deacetonation type organosiloxane compositions, are low in reactivity with moisture in the air and therefore are insufficient in curability.
  • the present invention has been devised based on the above circumstances, and an object of the present invention is to provide a room-temperature-curable organopolysiloxane composition, in particular, a dealcoholization-type room-temperature-curable organopolysiloxane composition, that is especially excellent in rapid curability, gives a cured product excellent in storage stability and durability, and can be advantageously produced on an industrial scale by using a versatile material.
  • the present inventors have conducted intensive research to achieve the object described above and, as a result, have found that the hydrolyzability of the alkoxy group in an alkoxysilyl group (including an unsubstituted or substituted alkoxysilyl group and an unsubstituted or substituted cycloalkoxysilyl group) is remarkably enhanced only when the alkoxysilyl group is adjacent to and bonded to a vinylene group (namely, an ethenylene group).
  • a hydrolyzable organic silicon compound represented by the general formula (2) below such as an organosilane having 2 alkoxysilyl-vinylene groups (alkoxysilyl-ethenylene groups) per molecule as a crosslinking agent (a curing agent)
  • a dealcoholization-type room-temperature-curable organopolysiloxane composition is obtained that is especially excellent in rapid curability and that gives a cured product excellent in storage stability and durability.
  • the room-temperature-curable organopolysiloxane composition can be advantageously produced on an industrial scale by using a versatile material (a diorganodichlorosilane, for example) as part of the starting material of the compound having alkoxysilyl-vinylene groups (alkoxysilyl-ethenylene groups).
  • a versatile material a diorganodichlorosilane, for example
  • the room-temperature-curable organopolysiloxane composition of the present invention is especially excellent in rapid curability in the air at room temperature and even after stored for 6 months, for example, it still rapidly cures upon exposure to the air and gives excellent physical properties. Therefore, the room-temperature-curable organopolysiloxane composition of the present invention is useful as a sealing agent, a coating agent, or an adhesive agent to be applied to a site where heat resistance, water resistance, or humidity resistance is required, and can be effectively used particularly where steam resistance or water resistance is required, such as in building applications and in applications as an adhesive agent for electrical and electronic uses.
  • the room-temperature-curable organopolysiloxane composition comprises a silicon compound represented by the general formula (2) having 2 alkoxysilyl-vinylene groups (alkoxysilyl-ethenylene groups) on a single silicon atom as the curing agent component (B), the room-temperature-curable organopolysiloxane composition of the present invention is especially excellent in rapid curability and can give a cured product that is excellent in storage stability and durability. Furthermore, the room-temperature-curable organopolysiloxane composition of the present invention can be advantageously produced on an industrial scale by using a versatile chlorosilane (a diorganodichlorosilane, for example) as a starting material of the component (B).
  • a versatile chlorosilane a diorganodichlorosilane, for example
  • a component (A) is a linear organopolysiloxane represented by the general formula (1) in which each end of the molecular chain is capped with a hydroxyl group that is bonded to a silicon atom (namely, a silanol group or a diorganohydroxysiloxy group).
  • the component (A) functions as the main component (the base polymer) of the composition of the present invention.
  • R 1 is a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, a plurality of R 1 may be the same as or different from each other, and n is an integer of 1 or greater.
  • the substituted or unsubstituted monovalent hydrocarbon group as R 1 in the general formula (1) above has about 1 to 20 carbon atoms, preferably about 1 to 10 carbon atoms, and more preferably about 1 to 8 carbon atoms and may be the same as or different from each other.
  • alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, and eicosyl group; cycloalkyl groups such as cyclopentyl group and cyclohexyl group; alkenyl groups such as vinyl group, allyl group, propenyl group, isopropenyl group, butenyl group,
  • the viscosity of the organopolysiloxane as the component (A) at 25°C is preferably from 10 to 1,000,000 mPa ⁇ s, more preferably from 50 to 500,000 mPa ⁇ s, particularly preferably from 100 to 100,000 mPa ⁇ s, and further preferably from 500 to 80,000 mPa ⁇ s.
  • the viscosity of the organopolysiloxane is preferably not lower than 10 mPa ⁇ s so as to readily obtain a coating that has excellent physical and mechanical strength, and the viscosity of the organopolysiloxane is preferably not higher than 1,000,000 mPa ⁇ s so as to prevent the viscosity of the resulting composition from being too high and to give excellent workability during use.
  • the viscosity is a numerical value measured with a rotational viscometer (BL-type, BH-type, BS-type, or Cone/Plate-type, for example; the same shall apply hereinafter).
  • n in the general formula (1) above (the number of, or the degree of polymerization of, difunctional diorganosiloxane units in the molecule) is usually from about 10 to 2,000, preferably from about 30 to 1,500, more preferably from about 50 to 1,200, and further preferably from about 100 to 1,000.
  • the degree of polymerization (or the molecular weight) is determined, for example, as a number average degree of polymerization (or a number average molecular weight) in terms of polystyrene measured by gel permeation chromatography (GPC) analysis in which toluene or the like is used as the developing solvent.
  • the organopolysiloxane as the component (A) can be used alone or as a combination of two or more of these.
  • the content of the organopolysiloxane as the component (A) in the room-temperature-curable organopolysiloxane composition of the present invention is preferably 99 to 20% by mass and particularly preferably 95 to 50% by mass.
  • a component (B) is a hydrolyzable organic silicon compound represented by the general formula (2) having 2 alkoxysilyl-vinylene groups (alkoxysilyl-ethenylene groups) on a single silicon atom.
  • the component (B) functions as a curing agent (a crosslinking agent) in the composition of the present invention.
  • the component (B) contributes to rapid curability of the composition and gives a cured product (silicone rubber) that is excellent in humidity resistance.
  • R 1 is a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, a plurality of R 1 may be the same as or different from each other, R 2 is an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or substituted cycloalkyl group having 3 to 20 carbon atoms, and a is an integer of 1 to 3.
  • the substituted or unsubstituted monovalent hydrocarbon group as R 1 in the general formula (2) above has about 1 to 20 carbon atoms, preferably about 1 to 10 carbon atoms, and more preferably about 1 to 8 carbon atoms and may be the same as or different from each other.
  • alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, and eicosyl group; cycloalkyl groups such as cyclopentyl group and cyclohexyl group; alkenyl groups such as vinyl group, allyl group, propenyl group, isopropenyl group, butenyl group,
  • the unsubstituted or substituted alkyl group as R 2 has about 1 to 20 carbon atoms, preferably about 1 to 6 carbon atoms, and more preferably about 1 to 4 carbon atoms. Specific examples thereof include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, and eicosyl group.
  • the unsubstituted or substituted cycloalkyl group has about 3 to 20 carbon atoms, preferably about 4 to 8 carbon atoms, and more preferably about 5 to 6 carbon atoms. Specific examples thereof include cyclopentyl group and cyclohexyl group.
  • part or all of the hydrogen atoms in the group may be substituted with a halogen atom such as F, Cl, or Br or with a group such as cyano group, and examples of such substituted groups include halogen-substituted alkyl groups such as 3-chloropropyl group and 3,3,3-trifluoropropyl group as well as 2-cyanoethyl group.
  • R 2 is preferably methyl group or ethyl group and particularly preferably methyl group in terms of hydrolyzability and the like.
  • the hydrolyzable organic silicon compound represented by the general formula (2) as the component (B) is used primarily as a curing agent (a crosslinking agent).
  • a curing agent a crosslinking agent
  • Each a in the general formula (2) is independently an integer of 1 to 3 and in terms of curability, it is preferably 2 or 3.
  • a hydrolyzable organic silicon compound having 3 alkoxy groups, such as 3 methoxy groups, on a single silicon atom of the molecule means that the hydrolyzable organic silicon compound has 2 trifunctional alkoxysilane moieties per molecule.
  • Such a hydrolyzable organic silicon compound is useful as a curing agent (crosslinking agent) for use in dealcoholization-type silicone RTV (room-temperature-curable organopolysiloxane compositions).
  • crosslinking agent room-temperature-curable organopolysiloxane compositions.
  • the silicon-containing compound having 2 alkoxysilyl-vinylene groups (alkoxysilyl-ethenylene groups) on a single silicon atom as the component (B) can be easily produced by, for example, addition reaction, namely, hydrosilylation reaction of a silane having 2 ethynyl groups on a single silicon atom with 2 alkoxyhydrosilanes.
  • This reaction is represented by the reaction formula [1] below, for example. wherein R 1 , R 2 , and a are the same as those defined for the general formula (2) above.
  • the catalyst for use in the addition reaction for adding alkoxyhydrosilanes may be a catalyst based on a metal of the platinum group, such as a platinum-based catalyst, a palladium-based catalyst, a rhodium-based catalyst, or a ruthenium-based catalyst, among which a platinum-based catalyst is particularly preferable.
  • the platinum-based catalyst include platinum black, ones composed of solid platinum supported on a carrier such as alumina or silica, chloroplatinate, alcohol-denatured chloroplatinate, complexes of chloroplatinate and an olefin, and complexes of platinum and vinylsiloxane.
  • the amount of platinum used in the catalyst may be a so-called catalytic amount, and when the catalyst is used for alkoxyhydrosilanes, for example, the mass of platinum can be from 0.1 to 1,000 ppm and, in particular, from 0.5 to 100 ppm in terms of a metal of the platinum group.
  • This reaction can be conducted without using a solvent, but alternatively, an appropriate solvent such as toluene or xylene can be used, if necessary, as long as no adverse influence is exerted on the addition reaction.
  • organic silicon compound of the general formula (2) having 2 alkoxysilyl-vinylene groups on a single silicon atom include ones represented by the following structural formulae. These compounds can be used alone or as a combination of two or more of these as the component (B) of the present invention.
  • the amount of the hydrolyzable organic silicon compound as the component (B) is from 0.1 to 30 parts by mass, preferably from 0.5 to 20 parts by mass, and more preferably from 3 to 15 parts by mass based on 100 parts by mass of the component (A). If the amount is smaller than 0.1 parts by mass, an adequate level of crosslinks may not be formed and, as a result, the resulting composition may not have the intended level of rapid curability. If the amount is greater than 30 parts by mass, the mechanical properties such as rubber-like properties may be poor. Either case may be economically disadvantageous.
  • a component (C) is a hydrolyzable silane and/or a partial hydrolysis-condensation product thereof except for the component (B) and is a crosslinking agent.
  • the component (C) is an optional component added as needed.
  • Specific examples of the component (C) include ethyl silicate, propyl silicate, methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, methyltris(methoxyethoxy) silane, vinyltris(methoxyethoxy) silane, methyltripropenoxysilane, phenyltripropenoxysilane, and partial hydrolysis-condensation products thereof. These can be used alone or as a combination of two or more of these.
  • the amount of the component (C) is usually from 0 to 30 parts by mass, preferably from 0.1 to 20 parts by mass, and more preferably from 0.5 to 15 parts by mass based on 100 parts by mass of the component (A). If the amount is greater than 30 parts by mass, the resulting cured product may be too hard, which is economically disadvantageous.
  • a component (D) is a curing catalyst and is used to facilitate the hydrolysis-condensation reaction between the composition of the present invention and moisture in the air.
  • the curing catalyst as the component (D) is a common curing catalyst.
  • the component (D) can be a known curing catalyst that is typically contained in a room-temperature-curable silicone rubber composition that cures in the presence of moisture.
  • curing catalyst as the component (D) examples include, but are not limited to, organic metal compounds, for example, alkyltin ester compounds such as dibutyltin diacetate, dibutyltin dilaurate, and dibutyltin dioctoate, titanic acid esters or titanium chelate compounds such as tetraisopropoxytitanium, tetra n-butoxytitanium, tetrakis(2-ethylhexoxy)titanium, dipropoxybis(acetylacetonato)titanium, and titanium isopropoxyoctylene glycol, zinc naphthenate, zinc stearate, zinc-2-ethyloctoate, iron-2-ethylhexoate, cobalt-2-ethylhexoate, manganese-2-ethylhexoate, cobalt naphthenate, alcoholate aluminum compounds such as aluminum isopropylate and aluminum secondary buty
  • the amount of the curing catalyst used may be a so-called catalytic amount.
  • the amount of the component (D) added is preferably from 0.001 to 20 parts by mass, particularly preferably from 0.005 to 10 parts by mass, and further preferably from 0.01 to 5 parts by mass based on 100 parts by mass of the organopolysiloxane as the component (A). If the amount is smaller than 0.001 parts by mass, excellent curability cannot be obtained and therefore the curing rate decreases. If the amount is greater than 20 parts by mass, the composition cures too rapidly, leading to a potential decrease in the time period during which the applied composition is still workable and to a potential deterioration in the mechanical properties of the resulting rubber.
  • a component (E) is a filler (an inorganic filler and/or an organic resin filler), which is an optional component added as needed for providing sufficient mechanical strength to the cured product of the composition.
  • the filler can be a known filler, and examples thereof include silica fine powder, fumed silica, precipitated silica, silicas having a hydrophobic surface obtained by surface treatment of these silicas with an organic silicon compound, glass beads, glass balloons, transparent resin beads, silica aerogel, diatomaceous earth, metal oxides such as iron oxide, zinc oxide, titanium oxide, and fumed metal oxides, wet silica or wet silica subjected to surface treatment with silane, quartz powder, carbon black, talc, zeolite, bentonite, and other reinforcing agents, asbestos, glass fiber, carbon fiber, metal carbonates such as calcium carbonate, magnesium carbonate, and zinc carbonate, asbestos, glass wool, fine powder mica, fused silica powder, and powders of synthetic resins such as polys
  • the amount of the component (E) added is from 0 to 1000 parts by mass, preferably from 0 to 400 parts by mass, particularly preferably from 0.1 to 200 parts by mass, and especially preferably from 0.5 to 200 parts by mass based on 100 parts by mass of the component (A). If the amount is greater than 1000 parts by mass, not only the viscosity of the resulting composition increases to impair workability, but also the cured product has low rubber-like strength and therefore is less likely to have rubber-like elasticity. Use of the component (E) can give sufficient mechanical strength to the cured product.
  • a component (F) is an adhesion promoter, which is an optional component added as needed for providing sufficient adhesion to the cured product of the composition.
  • the adhesion promoter a silane coupling agent such as a hydrolyzable silane containing a functional group
  • a known adhesion promoter can be suitably used. Examples thereof include vinylsilane coupling agents, (meth)acrylic silane coupling agents, epoxysilane coupling agents, aminosilane coupling agents, and mercaptosilane coupling agents.
  • Specific examples thereof include vinyltris( ⁇ -methoxyethoxy)silane, ⁇ -methacryloxypropyltrimethoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, N- ⁇ -(aminoethyl) ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, 3-2-(aminoethylamino)propyltrimethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, and isocyanate silane.
  • aminosilanes such as ⁇ -aminopropyltriethoxysilane and 3-2-(aminoethylamino)propyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, epoxy silanes such as ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and isocyanate silane are particularly preferable.
  • the amount of the component (F) added is from 0 to 30 parts by mass, preferably from 0.1 to 30 parts by mass, and particularly preferably from 0.5 to 20 parts by mass based on 100 parts by mass of the component (A).
  • the component (F) may be omitted.
  • a component (G) is an organopolysiloxane, which is an optional component added as needed.
  • the component (G) is represented by the general formula (3) below, and is a linear diorganopolysiloxane (a so-called non-functional silicone oil) having no functional group, within the molecule, that is capable of being involved with condensation reaction (in other words, the linear diorganopolysiloxane does not become involved with condensation-curing reaction of the composition).
  • R 1 is a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, a plurality of R 1 may be the same as or different from each other, and m is an integer of 1 to 2000.
  • the substituted or unsubstituted hydrocarbon group as R 1 in the general formula (3) above has 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms and may be the same as or different from each other.
  • Examples thereof can include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, and eicosyl group; cycloalkyl groups such as cyclopentyl group and cyclohexyl group; alkenyl groups such as vinyl group, allyl group, propenyl group, isopropenyl group, butenyl group,
  • the viscosity of the organopolysiloxane as the component (G) at 25°C is preferably from 0.65 to 1,000,000 mPa ⁇ s, more preferably from 30 to 500,000 mPa ⁇ s, particularly preferably from 50 to 100,000 mPa ⁇ s, and especially preferably from 100 to 80,000 mPa ⁇ s.
  • the viscosity of the organopolysiloxane is preferably not lower than 10 mPa ⁇ s so as to readily obtain a coating that has excellent physical and mechanical strength, and the viscosity of the organopolysiloxane is preferably not higher than 1,000,000 mPa ⁇ s so as to prevent the viscosity of the resulting composition from being too high and to give excellent workability during use.
  • the viscosity is a numerical value measured with a rotational viscometer.
  • m in the formula (3) above is an integer of 1 to 2000 and for the same reason as above, it is desirable that m is preferably an integer of about 10 to 1,500, an integer of about 30 to 1,200, and more preferably an integer of about 50 to 1,000.
  • the amount of the component (G) added is typically from 0 to 100 parts by mass, preferably from 0.1 to 80 parts by mass, more preferably from 0.5 to 75 parts by mass, further preferably from 5 to 70 parts by mass, and especially preferably from 10 to 60 parts by mass based on 100 parts by mass of the component (A).
  • the component (G) is not required.
  • the amount of the component (G) is greater than 100 parts by mass, rubber-like properties may be poor.
  • the room-temperature-curable organopolysiloxane composition of the present invention can further comprise, as its additives, known additives including a pigment, a dye, an anti-aging agent, an antioxidant, an antistatic agent, and a flame retardant such as antimony oxide and chlorinated paraffin.
  • the room-temperature-curable organopolysiloxane composition of the present invention can further comprise a thixotropy enhancer, such as a polyether, as well as a fungicide and an antimicrobial.
  • the room-temperature-curable organopolysiloxane composition of the present invention can be obtained by homogeneously mixing together the components described above and the various additives described above each in a predetermined amount in a dry atmosphere.
  • the room-temperature-curable organopolysiloxane composition cures while being left at room temperature.
  • the mouolding method and the curing conditions for example, can be known method and conditions that are selected according to the kind of the composition.
  • the room-temperature-curable organopolysiloxane composition of the present invention thus obtained cures rapidly at room temperature upon coming into contact with moisture in the air and gives a rubber-like elastic cured product excellent in heat resistance, weather resistance, properties at low temperatures, and adhesion to various base materials, in particular, metals.
  • the composition of the present invention is particularly excellent in storage stability and in curability and even after stored for 6 months, for example, it still cures rapidly upon exposure to the air and gives a cured product that has excellent physical properties as described above.
  • the composition of the present invention generates no toxic gas or corrosive gas upon curing and causes no rust on the surface to which the composition is applied.
  • the composition does not cause electrical contact failures in electrical and electronic components and, therefore, the composition is useful as an insulator and an adhesive compound for electrical and electronic components and can be widely used as a sealing agent, a coating agent, a coating agent, and a mold release agent for various base materials and also as a fiber-treatment agent.
  • the composition can give various moulded products that are excellent in heat resistance and weather resistance.
  • part(s) refers to "part(s) by mass” and the viscosity is a value measured at 25°C with a rotational viscometer.
  • the silicon-containing compound having 2 alkoxysilyl-vinylene groups on a single silicon atom as the component (B) is synthesized by the following method.
  • a composition was prepared in the same manner as in Example 1 except that 6.6 parts of bis(trimethoxysilyl-vinylene)diphenylsilane obtained in Synthesis Example 2 was used instead of the bis(trimethoxysilyl-vinylene)dimethylsilane.
  • compositions were prepared in the same manner as in Examples 1 to 3 except that 4.1 parts of vinyltrimethoxysilane [the silicon compound represented by the structural formula (4) below] was used instead of the bis(trimethoxysilyl-vinylene)dimethylsilane.
  • compositions were prepared in the same manner as in Examples 1 to 3 except that 3.8 parts of methyltrimethoxysilane [the silicon compound represented by the structural formula (5) below] was used instead of the bis(trimethoxysilyl-vinylene)dimethylsilane.
  • a composition was prepared in the same manner as in Example 1 except that 4.5 parts of 1,6-bis(trimethoxysilyl)hexane [the silicon compound represented by the structural formula (6) below] was used instead of the bis(trimethoxysilyl-vinylene)dimethylsilane.
  • compositions prepared in Examples 1 to 4 and Comparative Examples 1 to 7 were subjected to measurement of tack free time.
  • compositions prepared in Examples 1 to 4 and Comparative Examples 1 to 7 immediately after preparation were each extruded into a sheet with a thickness of 2 mm.
  • the resulting sheet was exposed to the air at 23 ⁇ 2°C and 50 ⁇ 5%RH, followed by being left in the same atmosphere for 7 days.
  • the resulting cured product was subjected to measurement of physical properties (initial physical properties) in conformity with JIS K-6249. Hardness was measured with a Durometer A, which is a hardness tester in conformity with JIS K-6249.
  • Table 1 shows the results of Examples 1 and 4 and Comparative Examples 1, 4, and 7;
  • Table 2 shows the results of Example 2 and Comparative Examples 2 and 5; and
  • Table 3 shows the results of Example 3 and Comparative Examples 3 and 6.
  • the room-temperature-curable organopolysiloxane composition cures rapidly and gives a cured product excellent in durability.
  • compositions prepared in Examples 5 to 7 were subjected to measurement of tack free time.
  • each of the compositions prepared in Examples 5 to 7 immediately after preparation was extruded into a sheet with a thickness of 2 mm.
  • the resulting sheet was exposed to the air at 23°C and 50%RH, followed by being left in the same atmosphere for 7 days.
  • the resulting cured product was subjected to measurement of physical properties (initial physical properties) in conformity with JIS K-6249. Hardness was measured with a Durometer A, which is a hardness tester in conformity with JIS K-6249.
  • Table 4 shows the results of Examples 5 to 7. [Table 4] Measurement results Ex. 5 Ex. 6 Ex. 7 Tack free time (minute) 3 3 5 Initial Hardness (Durometer A) 45 45 41 RTV Elongation (%) 180 160 170 7 days Tensile strength (MPa) 2.22 1.95 1.62 Humidity resistance Hardness (Durometer A) 40 40 39 85°C/85%RH Elongation (%) 175 190 170 7 days Tensile strength (MPa) 1.71 1.42 1.26 Heat resistance Hardness (Durometer A) 48 44 44 150°C Elongation (%) 165 175 165 10 days Tensile strength (MPa) 2.12 1.88 1.99
  • the room-temperature-curable organopolysiloxane composition of the present invention cures rapidly and gives a cured product excellent in durability.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Sealing Material Composition (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Claims (7)

  1. Bei Zimmertemperatur härtbare Organopolysiloxanzusammensetzung, umfassend die unten angegebenen Komponenten (A), (B) und (D):
    (A) ein Organopolysiloxan der folgenden allgemeinen Formel (1):
    Figure imgb0022
     wobei R1 ein Wasserstoffatom oder eine unsubstituierte oder substituierte einwertige Kohlenwasserstoffgruppe mit 1 bis 20 Kohlenstoffatomen ist, eine Mehrzahl von R1 gleich oder voneinander verschieden sein können, und n eine Ganzzahl von 1 oder höher ist;
    (B) eine organische Siliziumverbindung der folgenden allgemeinen Formel (2) enthaltend zwei Silyl-Vinylengruppen auf einem einzigen Siliziumatom, wobei eine Menge der Komponente (B) 0,1 bis 30 Massenteile bezogen auf 100 Massenteile der Komponente (A) beträgt:
    Figure imgb0023
     wobei R1 ein Wasserstoffatom oder eine unsubstituierte oder substituierte einwertige Kohlenwasserstoffgruppe mit 1 bis 20 Kohlenstoffatomen ist, eine Mehrzahl von R1 gleich oder voneinander verschieden sein können, R2 eine unsubstituierte oder substituierte Alkylgruppe mit 1 bis 20 Kohlenstoffatomen oder eine unsubstituierte oder substituierte Cycloalkylgruppe mit 3 bis 20 Kohlenstoffatomen ist, und a eine Ganzzahl von 1 bis 3 ist; und
    (D) einen Härtekatalysator, wobei eine Menge der Komponente (D) 0,001 bis 20 Massenteile bezogen auf 100 Massenteile der Komponente (A) beträgt.
  2. Bei Zimmertemperatur härtbare Organopolysiloxanzusammensetzung nach Anspruch 1, ferner umfassend (C) ein hydrolysierbares Silan und/oder ein teilweises Hydrolyse-Kondensationsprodukt davon bis auf die Komponente (B), wobei eine Menge der Komponente (C) 0,1 bis 30 Massenteile bezogen auf 100 Massenteile der Komponente (A) beträgt.
  3. Bei Zimmertemperatur härtbare Organopolysiloxanzusammensetzung nach Anspruch 1 oder 2, ferner umfassend (E) einen Füllstoff, wobei eine Menge der Komponente (E) 0,1 bis 1000 Massenteile bezogen auf 100 Massenteile der Komponente (A) beträgt.
  4. Bei Zimmertemperatur härtbare Organopolysiloxanzusammensetzung nach einem der Ansprüche 1 bis 3, ferner umfassend (F) einen Haftvermittler, wobei eine Menge der Komponente (F) 0,1 bis 30 Massenteile bezogen auf 100 Massenteile der Komponente (A) beträgt.
  5. Bei Zimmertemperatur härtbare Organopolysiloxanzusammensetzung nach einem der Ansprüche 1 bis 4, ferner umfassend (G) ein Organopolysiloxan der allgemeinen Formel (3), wobei eine Menge der Komponente (G) 0,1 bis 100 Massenteile bezogen auf 100 Massenteile der Komponente (A) beträgt:
    Figure imgb0024
     wobei R1 ein Wasserstoffatom oder eine unsubstituierte oder substituierte einwertige Kohlenwasserstoffgruppe mit 1 bis 20 Kohlenstoffatomen ist, eine Mehrzahl von R1 gleich oder voneinander verschieden sein können, und m eine Ganzzahl von 1 bis 2000 ist.
  6. Dichtungsmittel, Beschichtungsmittel oder Klebemittel, umfassend die bei Zimmertemperatur härtbare Organopolysiloxanzusammensetzung nach einem der Ansprüche 1 bis 5.
  7. Formprodukt umfassend ein gehärtetes Produkt aus der bei Zimmertemperatur härtbaren Organopolysiloxanzusammensetzung nach einem der Ansprüche 1 bis 5.
EP15809931.7A 2014-06-16 2015-05-27 Bei zimmertemperatur härtbare organopolysiloxanzusammensetzung und formprodukt mit gehärtetem produkt aus der besagten, bei zimmertemperatur härtbaren organopolysiloxanzusammensetzung Active EP3156458B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014123070 2014-06-16
PCT/JP2015/065317 WO2015194340A1 (ja) 2014-06-16 2015-05-27 室温硬化性オルガノポリシロキサン組成物及び該室温硬化性オルガノポリシロキサン組成物の硬化物である成形物

Publications (3)

Publication Number Publication Date
EP3156458A1 EP3156458A1 (de) 2017-04-19
EP3156458A4 EP3156458A4 (de) 2018-01-24
EP3156458B1 true EP3156458B1 (de) 2019-06-26

Family

ID=54935332

Family Applications (1)

Application Number Title Priority Date Filing Date
EP15809931.7A Active EP3156458B1 (de) 2014-06-16 2015-05-27 Bei zimmertemperatur härtbare organopolysiloxanzusammensetzung und formprodukt mit gehärtetem produkt aus der besagten, bei zimmertemperatur härtbaren organopolysiloxanzusammensetzung

Country Status (6)

Country Link
US (1) US10040923B2 (de)
EP (1) EP3156458B1 (de)
JP (1) JP6497390B2 (de)
KR (1) KR102326223B1 (de)
CN (1) CN106459586B (de)
WO (1) WO2015194340A1 (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106255696A (zh) * 2014-04-25 2016-12-21 信越化学工业株式会社 新颖的含有双(烷氧基甲硅烷基‑亚乙烯)基的硅化合物及其制备方法
EP3279267B1 (de) 2015-04-03 2019-09-18 Shin-Etsu Chemical Co., Ltd. Bei raumtemperatur härtbare organopolysiloxanzusammensetzung und formkörper als gehärtetes objekt aus dieser zusammensetzung
KR102619534B1 (ko) * 2016-04-26 2023-12-29 신에쓰 가가꾸 고교 가부시끼가이샤 실온 경화성 조성물, 실링재, 및 물품
EP3456786B1 (de) * 2016-05-09 2021-05-26 Shin-Etsu Chemical Co., Ltd. Bei raumtemperatur härtbare organopolysiloxanzusammensetzung und mit gehärtetem objekt aus der besagten zusammensetzung beschichteter sockel
CA3026619C (en) * 2016-06-28 2024-07-02 Threebond Co., Ltd. Composition of hardening resin, fuel cell, and sealing method
CN107523259B (zh) * 2017-10-12 2020-08-11 济南大学 一种α-570偶联剂改性的有机硅密封胶的制备
WO2019077942A1 (ja) * 2017-10-17 2019-04-25 信越化学工業株式会社 室温硬化性組成物、シーリング材及び物品
JP7088211B2 (ja) * 2017-12-15 2022-06-21 信越化学工業株式会社 室温湿気硬化型シリコーンゲル組成物及びその硬化物並びに物品
CN108034404B (zh) * 2018-01-22 2020-12-15 黑龙江省科学院石油化学研究院 一种高韧性有机/无机杂化耐高温胶黏剂
CN108314987B (zh) * 2018-02-12 2021-01-29 黑龙江奥星能源科技有限公司 一种含有石墨粉的耐高温胶粘剂及其制备方法
EP4180488A4 (de) * 2020-07-07 2024-08-07 Shin-Etsu Chemical Co., Ltd. Bei raumtemperatur schnellhärtende zweikomponentige organopolysiloxanzusammensetzung, gehärtetes produkt daraus und artikel
CN112481000B (zh) * 2020-11-27 2022-04-22 武汉善达化工有限公司 一种用于耐火材料的环保脱模剂及其制备和使用方法
KR20240089740A (ko) * 2021-10-19 2024-06-20 신에쓰 가가꾸 고교 가부시끼가이샤 실온 경화성 오르가노폴리실록산 조성물, 접착제, 시일제 및 코팅제

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6059917B2 (ja) * 1977-12-21 1985-12-27 東芝シリコ−ン株式会社 シス−１，２−ジシリルアルケン化合物
JPS5543119A (en) 1978-09-20 1980-03-26 Sws Silicones Corp Titanium ester contained vulcanizable organopolysiloxane composition and its manufacture
JPH0739547B2 (ja) 1992-01-10 1995-05-01 東レ・ダウコーニング・シリコーン株式会社 室温硬化性オルガノポリシロキサン組成物
JPH07331076A (ja) 1994-06-03 1995-12-19 Shin Etsu Chem Co Ltd 室温硬化性オルガノポリシロキサン組成物
JP3927643B2 (ja) 1997-04-01 2007-06-13 日本たばこ産業株式会社 分岐αデキストリンに親油性香料を包接指せた加香剤を用いた喫煙物品
JP4821958B2 (ja) * 2005-05-13 2011-11-24 信越化学工業株式会社 室温硬化性オルガノポリシロキサン組成物
CN101568597B (zh) * 2006-12-25 2012-01-18 中国涂料株式会社 固化性组合物、防污涂料组合物、防污涂膜、带防污涂膜的基材及基材的防污方法
JP5817626B2 (ja) * 2012-04-04 2015-11-18 信越化学工業株式会社 室温硬化性オルガノポリシロキサン組成物
CN104870524B (zh) 2012-12-20 2017-07-11 信越化学工业株式会社 烷氧基硅烷基‑亚乙基末端有机硅氧烷聚合物的制造方法、室温固化性组合物及其固化物
JP5997778B2 (ja) 2012-12-20 2016-09-28 信越化学工業株式会社 新規アルコキシシリル−エチレン基末端ケイ素含有化合物、室温硬化性オルガノポリシロキサン組成物、及び該組成物を硬化して得られる成形物
EP2998287B1 (de) * 2013-05-16 2023-07-19 Shin-Etsu Chemical Co., Ltd. Aluminiumchelatverbindung und bei raumtemperatur härtbare harzzusammensetzung damit
CN105829449B (zh) * 2013-12-17 2019-07-05 信越化学工业株式会社 多成分系室温固化性有机聚硅氧烷组合物和该组合物的固化物以及包括该固化物的成型物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Also Published As

Publication number Publication date
CN106459586B (zh) 2019-11-26
US20170130031A1 (en) 2017-05-11
KR102326223B1 (ko) 2021-11-15
US10040923B2 (en) 2018-08-07
CN106459586A (zh) 2017-02-22
WO2015194340A1 (ja) 2015-12-23
JP6497390B2 (ja) 2019-04-10
KR20170018408A (ko) 2017-02-17
EP3156458A4 (de) 2018-01-24
JPWO2015194340A1 (ja) 2017-06-01
EP3156458A1 (de) 2017-04-19

Similar Documents

Publication Publication Date Title
EP3156458B1 (de) Bei zimmertemperatur härtbare organopolysiloxanzusammensetzung und formprodukt mit gehärtetem produkt aus der besagten, bei zimmertemperatur härtbaren organopolysiloxanzusammensetzung
EP3085739B1 (de) Mehrkomponentige, bei raumtemperatur härtbare organopolysiloxanzusammensetzung, gehärtetes produkt aus der besagten zusammensetzung und geformtes produkt mit besagtem gehärteten produkt
US9475969B2 (en) Organopolysiloxane compound having ethynyl groups, method for preparing linear organopolysiloxane compound having ethynyl groups at both terminals of molecular chain, method for preparing organopolysiloxane polymer having alkoxysilyl-ethylene group at terminal, room temperature curable composition and molded product which is cured product thereof
US20150315438A1 (en) Novel silicon-containing compound having alkoxysilyl-ethylene group at its terminal, room temperature-curable organopolysiloxane composition, and molded product obtained by curing the composition
JP6747507B2 (ja) 室温硬化性組成物、シーリング材並びに物品
CN107429061B (zh) 室温固化性有机聚硅氧烷组合物和为该组合物的固化物的成型物
JP2024117823A (ja) 二成分型室温速硬化性オルガノポリシロキサン組成物、該組成物の硬化物及び物品、並びに室温速硬化性オルガノポリシロキサン組成物の硬化方法
JP6760223B2 (ja) 室温硬化性オルガノポリシロキサン組成物、およびこれを含有するシール剤、コーティング剤、接着剤、成形物
US10428183B2 (en) Room temperature-curable resin composition containing an aluminum chelate compound
EP3705535B1 (de) Organopolysiloxanzusammensetzung und organische siliziumverbindung und verfahren zu ihrer herstellung
WO2023068094A1 (ja) 室温硬化性オルガノポリシロキサン組成物、接着剤、シール剤及びコーティング剤
WO2016035427A1 (ja) 新規有機チタン化合物、該有機チタン化合物の製造方法及び室温硬化性樹脂組成物
JP5915599B2 (ja) 室温硬化性樹脂組成物

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20170103

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
A4 Supplementary search report drawn up and despatched

Effective date: 20180104

RIC1 Information provided on ipc code assigned before grant

Ipc: C08L 83/06 20060101AFI20171220BHEP

Ipc: C08K 5/5425 20060101ALI20171220BHEP

Ipc: C09K 3/10 20060101ALI20171220BHEP

Ipc: C09J 183/06 20060101ALI20171220BHEP

Ipc: C09D 183/06 20060101ALI20171220BHEP

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

INTG Intention to grant announced

Effective date: 20180517

GRAJ Information related to disapproval of communication of intention to grant by the applicant or resumption of examination proceedings by the epo deleted

Free format text: ORIGINAL CODE: EPIDOSDIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

INTC Intention to grant announced (deleted)
GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

INTG Intention to grant announced

Effective date: 20181130

GRAJ Information related to disapproval of communication of intention to grant by the applicant or resumption of examination proceedings by the epo deleted

Free format text: ORIGINAL CODE: EPIDOSDIGR1

GRAL Information related to payment of fee for publishing/printing deleted

Free format text: ORIGINAL CODE: EPIDOSDIGR3

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

GRAR Information related to intention to grant a patent recorded

Free format text: ORIGINAL CODE: EPIDOSNIGR71

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

INTC Intention to grant announced (deleted)
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE PATENT HAS BEEN GRANTED

INTG Intention to grant announced

Effective date: 20190514

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: AT

Ref legal event code: REF

Ref document number: 1148236

Country of ref document: AT

Kind code of ref document: T

Effective date: 20190715

REG Reference to a national code

Ref country code: DE

Ref legal event code: R096

Ref document number: 602015032818

Country of ref document: DE

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: NL

Ref legal event code: MP

Effective date: 20190626

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: AL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: HR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: NO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190926

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

REG Reference to a national code

Ref country code: LT

Ref legal event code: MG4D

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: RS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190927

Ref country code: LV

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190926

REG Reference to a national code

Ref country code: AT

Ref legal event code: MK05

Ref document number: 1148236

Country of ref document: AT

Kind code of ref document: T

Effective date: 20190626

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: AT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20191028

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: SM

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20191026

Ref country code: IT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: TR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: PL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20200224

REG Reference to a national code

Ref country code: DE

Ref legal event code: R097

Ref document number: 602015032818

Country of ref document: DE

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG2D Information on lapse in contracting state deleted

Ref country code: IS

26N No opposition filed

Effective date: 20200603

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200531

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200531

REG Reference to a national code

Ref country code: BE

Ref legal event code: MM

Effective date: 20200531

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200527

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200527

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200531

REG Reference to a national code

Ref country code: DE

Ref legal event code: R082

Ref document number: 602015032818

Country of ref document: DE

Representative=s name: ZACCO LEGAL RECHTSANWALTSGESELLSCHAFT MBH, DE

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190626

REG Reference to a national code

Ref country code: FR

Ref legal event code: PLFP

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20250402

Year of fee payment: 11

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20250401

Year of fee payment: 11

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20250401

Year of fee payment: 11

REG Reference to a national code

Ref country code: DE

Ref legal event code: R082

Ref document number: 602015032818

Country of ref document: DE